Boyland–Sims氧化

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利用过硫酸钾在碱性条件下氧化苯胺，然后水解得到邻胺基苯酚的反应。氧化优先发生在邻位，有时会得到邻对位同时氧化的产物。苯酚类底物在相同条件下被氧化的反应被称为Elbs过硫酸盐氧化反应。Elbs氧化反应主要得到对位氧化产物。



反应机理


另外一种可能的机理是：


反应实例

【J. Am. Chem. Soc. 1967, 89, 2424-2428】



 Aq K2S2O8 (27 g, 100 mmol) in 700 mL H2O was added dropwise over 1 h to a mixture of 3,4-dichloroaniline 4 (16.2 g, 100 mmol), pyr (100 mL) and 100 mL 2N KOH. After 15 h of stirring at r.t., decantation and evaporation at 45 ℃ in vacuo gave a solid which was triturated with Et2O(5 X 200 mL). The remaining solid was triturated with MeOH (5 X 75 mL) and the combined liquids were evaporated to afford 7 g (41%) of 5 + 6. Purification by reverse phase HPLC provided 385 mg of

5, and 541 mg of 6.

【Bioorg. Med. Chem., 1992, 2, 1013】


【Organic Letters, 2013, 15, 2334-2337】


参考文献

1. Boyland, E.; Manson, D.; Sims, P. J. Chem. Soc. 1953, 3623-3628. Eric Boyland and Peter Sims were at the Royal Cancer Hospital in London, UK.

2. Boyland, E.; Sims, P. J. Chem. Soc. 1954, 980-985.

3. Behrman, E. J. J. Am. Chem. Soc. 1967, 89, 2424-2428.

4. Behrman, E. J.; Behrman, D. M. J. Org. Chem. 1978, 43, 4551-4552.

5. Srinivasan, C.; Perumal, S.; Arumugam, N. J. Chem. Soc., Perkin Trans. 2 1985, 1855-1858.

6. Behrman, E. J. Org. React. 1988, 35, 421-511. (Review).

7. Behrman, E. J. J. Org. Chem. 1992, 57, 2266-2270.

8. Behrman, E. J. Beilstein J. Org. Chem. 2006, 2, 22.

9. Behrman, E. J. Chem. Educator 2010, 15, 392-393.

10. Behrman, E. J. J. Phys. Chem. 2011, 115, 7863-


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